Synthesis of β-D-Ara-(1→2)-α-D-Ara-(1→5)-α-D-Ara trisaccharides as 2-azidoethyl and 4-(2-trifluoroacetamidoethoxy)phenyl glycosides related to the fragments of mycobacterial polysaccharides

Synthesis of β-D-Ara-(1→2)-α-D-Ara-(1→5)-α-D-Ara trisaccharides as 2-azidoethyl and 4-(2-trifluoroacetamidoethoxy)phenyl glycosides related to the fragments of mycobacterial polysaccharides Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2026, Volume: 568, Article number : 110015, Pages count : DOI: 10.1016/j.carres.2026.110015

Tags

glycosylation; D-arabinofuranose; silyl group; Mycobacterium tuberculosis

Authors

Novikov Dmitry S. ¹ , Abronina Polina I. ¹ , Zinin Alexander I. ¹ , Medvedeva Svetlana A. ¹ , Kolotyrkina Natalia G. ¹ , Kononov Leonid O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Two glycosides of β-D-Ara-(1→2)-α-D-Ara-(1→5)-α-D-Ara trisaccharide related to the fragments of mycobacterial polysaccharides with 4-(2-trifluoroacetamidoethoxy)phenyl and 2-azidoethyl aglycones, required for further conjugation with protein carriers and preparation of neoglycoconjugates, were synthesized using silylated (TIPS or TBDPS) Ara-β-(1→2)-Ara disaccharide thioglycosides as glycosyl donors. We found that the protective groups in glycosyl acceptor (benzoyl or 4-tert-butylbenzyl) and aglycone nature do not affect stereoselectivity of glycosylation with silylated Ara-β-(1→2)-Ara disaccharide glycosyl donors. Earlier we showed that TIPS-protected Ara-β-(1→2)-Ara disaccharide thioglycoside could be prepared by thiolysis of the corresponding 4-(3-chloropropoxy)phenyl glycoside in 50% yield. A study of thiolysis of different mono- and disaccharide substrates containing 4-(2-chloroethoxy)phenyl, 4-(2-azidoethoxy)phenyl and 4-methoxyphenyl aglycones revealed that the highest yield (95%) of the target p-tolyl thioglycoside can be achieved with TBDPS-protected Ara-β-(1→2)-Ara dissacharide with 4-methoxyphenyl aglycone.

Novikov D.S. , Abronina P.I. , Zinin A.I. , Medvedeva S.A. , Kolotyrkina N.G. , Kononov L.O.
Synthesis of β-D-Ara-(1→2)-α-D-Ara-(1→5)-α-D-Ara trisaccharides as 2-azidoethyl and 4-(2-trifluoroacetamidoethoxy)phenyl glycosides related to the fragments of mycobacterial polysaccharides
Carbohydrate Research. 2026. V.568. 110015 . DOI: 10.1016/j.carres.2026.110015 Scopus OpenAlex

Submitted:	May 12, 2026
Accepted:	Jun 24, 2026
Published online:	Jul 2, 2026

≡ Scopus:	2-s2.0-105043996109
≡ OpenAlex:	W7167018817